Halogen-containing alkaloids

Epibatidine is a chlorinated alkaloid that is secreted by the Ecuadorian frog Epipedobates anthonyi and poison dart frogs from the genus Ameerega. It was discovered by John W. Daly in 1974, but its structure was not fully elucidated until 1992. Whether epibatidine occurs naturally remains controversial due to challenges in conclusively identifying the compound from the limited samples collected by Daly. By the time that high-resolution spectrometry was used in 1991, there remained less than one milligram of extract from Daly's samples, raising concerns about possible contamination. Samples fro

Pyrrolnitrin (PRN) is a naturally occurring phenylpyrrole fungicide. Pseudomonas and Burkholderia species produce pyrrolnitrin from tryptophan as secondary metabolite. It is believed that the antifungal properties come from inhibition of electron transport system.

'''Palau'amine' is a toxic chlorinated alkaloid compound synthesized naturally by certain species of sea sponges. The name of the molecule derives from the island nation of Palau, near where the first sponge species discovered to produce it, Stylotella agminata, is found. It has since been isolated in other sponges, including Stylissa massa''.

chemical compound

5-Bromo-DMT, or 5-Br-DMT, also known as '5-bromo-N,N-dimethyltryptamine or by informal names like sea DMT or SpongeBob DMT', is a psychedelic drug and brominated indole alkaloid of the tryptamine family related to dimethyltryptamine (DMT). It is the 5-bromo derivative of DMT. The drug is naturally occurring in the sponges Smenospongia aurea and Smenospongia echina, as well as in Verongula rigida (0.00142% dry weight) alongside 5,6-dibromo-DMT (0.35% dry weight) and seven other alkaloids. It has been encountered as a novel designer drug.

Ageliferin is a chemical compound produced by some sponges. It was first isolated from Caribbean and then Okinawan marine sponges in the genus Agelas. It often co-exists with the related compound sceptrin and other similar compounds. It has antibacterial properties and can cause biofilms to dissolve. Total syntheses have been independently accomplished by the research groups of Phil S. Baran at the Scripps Research Institute, Chuo Chen at UT Southwestern Medical Center, Patrick Harran at UCLA, and Daisuke Urabe at Toyama Prefectural University.

Rebeccamycin (NSC 655649) is a weak topoisomerase I inhibitor isolated from Nocardia bacteria. It is structurally similar to staurosporine, but does not show any inhibitory activity against protein kinases. It shows significant antitumor properties in vitro (IC50=480nM against mouse B16 melanoma cells and IC50=500nM against P388 leukemia cells). It is an antineoplastic antibiotic and an intercalating agent.